4,5-Diphenyl-2-p-tolyl-1H-imidazol-3-ium nitrate.

In the cation of the title compound, C(22)H(19)N(2) (+)·NO(3) (-), the N atom in the 3-position of the imidazole is protonated. The three pendant aromatic rings are twisted from the plane of the imadazolium ring by dihedral angles of 38.1 (1), 43.74 (9) and 20.4 (1)°. In the crystal structure, N-H⋯O and N-H⋯(O,O) hydrogen bonds link the mol-ecules to form an infinite one-dimensional chain parallel to the c axis.

Related literature

For uses of imidazole derivatives, see: Dai & Fu (2008 ▶); Fu & Xiong (2008 ▶); Huang et al. (2008 ▶).

Experimental

Crystal data

C22H19N2 +·NO3 −

M = 373.40

Orthorhombic,

a = 8.442 (2) Å

b = 12.970 (3) Å

c = 17.098 (3) Å

V = 1872.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.35 × 0.25 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.955, T max = 1.000 (expected range = 0.934–0.978)

19745 measured reflections

4278 independent reflections

2714 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.143

S = 1.03

4278 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018789/im2112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018789/im2112Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H19N2+·NO3−	F(000) = 784
Mr = 373.40	Dx = 1.325 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2714 reflections
a = 8.442 (2) Å	θ = 3.1–27.5°
b = 12.970 (3) Å	µ = 0.09 mm−1
c = 17.098 (3) Å	T = 298 K
V = 1872.3 (6) Å3	Block, colorless
Z = 4	0.40 × 0.35 × 0.25 mm

Rigaku Mercury2 diffractometer	4278 independent reflections
Radiation source: fine-focus sealed tube	2714 reflections with I > 2σ(I)
graphite	Rint = 0.089
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD profile fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.955, Tmax = 1.000	l = −22→22
19745 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.288P] where P = (Fo2 + 2Fc2)/3
4278 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.3099 (3)	0.44418 (17)	0.66981 (13)	0.0415 (6)
H1A	0.2804	0.4503	0.7177	0.050*
N2	0.3114 (3)	0.45286 (18)	0.54570 (13)	0.0438 (6)
H2A	0.2827	0.4654	0.4984	0.053*
C16	0.0757 (3)	0.5305 (2)	0.60980 (17)	0.0409 (7)
C8	0.4517 (3)	0.4054 (2)	0.56608 (16)	0.0402 (7)
C19	−0.2150 (3)	0.6340 (2)	0.61119 (19)	0.0464 (7)
C7	0.4501 (3)	0.3994 (2)	0.64587 (15)	0.0368 (6)
C15	0.2268 (3)	0.4767 (2)	0.60831 (17)	0.0407 (7)
C6	0.5633 (3)	0.3576 (2)	0.70270 (15)	0.0389 (7)
C1	0.6475 (3)	0.2682 (2)	0.68690 (17)	0.0462 (7)
H1	0.6301	0.2329	0.6403	0.055*
C21	0.0283 (4)	0.5898 (2)	0.54664 (17)	0.0482 (7)
H21	0.0938	0.5955	0.5031	0.058*
C10	0.7240 (4)	0.3933 (2)	0.51284 (18)	0.0492 (8)
H10	0.7630	0.4213	0.5591	0.059*
C17	−0.0230 (3)	0.5248 (2)	0.67441 (17)	0.0483 (8)
H17	0.0068	0.4859	0.7177	0.058*
C9	0.5648 (3)	0.3741 (2)	0.50526 (16)	0.0406 (7)
C12	0.7709 (4)	0.3280 (3)	0.38461 (18)	0.0559 (8)
H12	0.8403	0.3138	0.3438	0.067*
C20	−0.1144 (4)	0.6400 (2)	0.54785 (18)	0.0499 (8)
H20	−0.1442	0.6793	0.5048	0.060*
C14	0.5107 (4)	0.3290 (3)	0.43701 (17)	0.0550 (8)
H14	0.4035	0.3142	0.4315	0.066*
C13	0.6136 (4)	0.3057 (3)	0.37721 (18)	0.0611 (9)
H13	0.5761	0.2749	0.3318	0.073*
C4	0.6997 (4)	0.3718 (3)	0.82531 (18)	0.0594 (9)
H4	0.7178	0.4068	0.8719	0.071*
C11	0.8262 (4)	0.3713 (3)	0.45231 (19)	0.0577 (9)
H11	0.9335	0.3860	0.4575	0.069*
C18	−0.1656 (3)	0.5769 (2)	0.67453 (17)	0.0475 (8)
H18	−0.2300	0.5733	0.7186	0.057*
C5	0.5878 (4)	0.4079 (2)	0.77306 (16)	0.0482 (8)
H5	0.5287	0.4662	0.7852	0.058*
C2	0.7562 (4)	0.2313 (3)	0.73960 (19)	0.0583 (9)
H2	0.8112	0.1708	0.7290	0.070*
C3	0.7842 (4)	0.2839 (3)	0.8083 (2)	0.0635 (9)
H3	0.8603	0.2600	0.8431	0.076*
C22	−0.3743 (4)	0.6851 (3)	0.6105 (2)	0.0662 (9)
H22A	−0.4143	0.6869	0.5580	0.099*
H22B	−0.3645	0.7542	0.6300	0.099*
H22C	−0.4460	0.6470	0.6431	0.099*
O3	0.1692 (3)	0.3887 (2)	0.80660 (12)	0.0721 (7)
N3	0.1779 (4)	0.4295 (2)	0.87181 (16)	0.0564 (7)
O2	0.1035 (4)	0.3954 (2)	0.92659 (14)	0.0901 (9)
O1	0.2677 (3)	0.5050 (2)	0.88344 (16)	0.0796 (8)

	U11	U22	U33	U12	U13	U23
N1	0.0432 (13)	0.0476 (14)	0.0338 (12)	0.0053 (12)	0.0035 (11)	−0.0016 (10)
N2	0.0445 (15)	0.0562 (15)	0.0306 (12)	0.0085 (12)	0.0007 (11)	0.0029 (11)
C16	0.0384 (15)	0.0424 (15)	0.0419 (16)	0.0045 (13)	−0.0010 (15)	−0.0022 (14)
C8	0.0360 (15)	0.0432 (16)	0.0413 (16)	0.0010 (14)	−0.0024 (13)	0.0032 (13)
C19	0.0426 (16)	0.0425 (15)	0.0541 (18)	0.0026 (14)	−0.0014 (16)	−0.0071 (15)
C7	0.0331 (14)	0.0398 (15)	0.0376 (15)	0.0001 (13)	0.0015 (12)	−0.0009 (12)
C15	0.0402 (15)	0.0446 (16)	0.0374 (16)	0.0030 (13)	0.0008 (14)	0.0038 (14)
C6	0.0367 (15)	0.0470 (16)	0.0330 (14)	−0.0035 (14)	0.0009 (12)	0.0024 (12)
C1	0.0410 (16)	0.0520 (17)	0.0456 (17)	0.0058 (15)	−0.0002 (14)	0.0000 (15)
C21	0.0508 (18)	0.0513 (17)	0.0426 (17)	0.0061 (16)	0.0029 (15)	0.0078 (14)
C10	0.0453 (17)	0.0503 (17)	0.0522 (18)	0.0002 (15)	−0.0004 (14)	−0.0071 (15)
C17	0.0475 (17)	0.0576 (18)	0.0396 (17)	0.0040 (15)	0.0006 (15)	0.0048 (14)
C9	0.0432 (16)	0.0400 (15)	0.0387 (15)	0.0063 (14)	0.0025 (13)	0.0037 (13)
C12	0.057 (2)	0.068 (2)	0.0424 (18)	0.0168 (17)	0.0100 (17)	−0.0034 (17)
C20	0.057 (2)	0.0465 (17)	0.0460 (18)	0.0091 (16)	−0.0023 (15)	0.0046 (15)
C14	0.0473 (19)	0.075 (2)	0.0425 (18)	0.0035 (17)	−0.0005 (15)	−0.0022 (16)
C13	0.062 (2)	0.082 (2)	0.0386 (18)	0.0152 (19)	−0.0057 (16)	−0.0114 (17)
C4	0.070 (2)	0.068 (2)	0.0398 (17)	−0.014 (2)	−0.0128 (17)	0.0063 (16)
C11	0.0453 (19)	0.062 (2)	0.066 (2)	−0.0002 (17)	0.0112 (17)	−0.0041 (18)
C18	0.0433 (16)	0.0556 (18)	0.0435 (17)	−0.0022 (15)	0.0109 (14)	−0.0055 (15)
C5	0.0542 (19)	0.0508 (18)	0.0396 (17)	−0.0052 (17)	−0.0005 (15)	0.0020 (14)
C2	0.0446 (19)	0.067 (2)	0.063 (2)	0.0116 (17)	−0.0022 (17)	0.0084 (18)
C3	0.0506 (19)	0.083 (2)	0.057 (2)	−0.0026 (19)	−0.0162 (17)	0.023 (2)
C22	0.0498 (19)	0.064 (2)	0.085 (2)	0.0097 (16)	−0.002 (2)	−0.001 (2)
O3	0.0800 (17)	0.1055 (19)	0.0309 (12)	0.0005 (15)	−0.0044 (12)	−0.0037 (13)
N3	0.0602 (18)	0.0612 (18)	0.0477 (17)	0.0134 (15)	−0.0019 (15)	0.0046 (14)
O2	0.142 (3)	0.0865 (19)	0.0423 (13)	−0.011 (2)	0.0201 (16)	0.0009 (14)
O1	0.0746 (17)	0.0722 (16)	0.092 (2)	−0.0013 (15)	0.0004 (17)	−0.0109 (15)

N1—C15	1.333 (3)	C17—H17	0.9300
N1—C7	1.381 (3)	C9—C14	1.383 (4)
N1—H1A	0.8600	C12—C13	1.364 (5)
N2—C15	1.324 (3)	C12—C11	1.369 (4)
N2—C8	1.379 (4)	C12—H12	0.9300
N2—H2A	0.8600	C20—H20	0.9300
C16—C21	1.385 (4)	C14—C13	1.375 (4)
C16—C17	1.386 (4)	C14—H14	0.9300
C16—C15	1.454 (4)	C13—H13	0.9300
C8—C7	1.367 (4)	C4—C3	1.376 (5)
C8—C9	1.469 (4)	C4—C5	1.382 (4)
C19—C18	1.377 (4)	C4—H4	0.9300
C19—C20	1.379 (4)	C11—H11	0.9300
C19—C22	1.499 (4)	C18—H18	0.9300
C7—C6	1.467 (4)	C5—H5	0.9300
C6—C5	1.384 (4)	C2—C3	1.378 (5)
C6—C1	1.387 (4)	C2—H2	0.9300
C1—C2	1.372 (4)	C3—H3	0.9300
C1—H1	0.9300	C22—H22A	0.9600
C21—C20	1.370 (4)	C22—H22B	0.9600
C21—H21	0.9300	C22—H22C	0.9600
C10—C9	1.372 (4)	O3—N3	1.236 (3)
C10—C11	1.377 (4)	N3—O2	1.212 (3)
C10—H10	0.9300	N3—O1	1.254 (4)
C17—C18	1.380 (4)
C15—N1—C7	110.5 (2)	C13—C12—C11	119.8 (3)
C15—N1—H1A	124.7	C13—C12—H12	120.1
C7—N1—H1A	124.7	C11—C12—H12	120.1
C15—N2—C8	111.3 (2)	C21—C20—C19	121.8 (3)
C15—N2—H2A	124.4	C21—C20—H20	119.1
C8—N2—H2A	124.4	C19—C20—H20	119.1
C21—C16—C17	118.5 (3)	C13—C14—C9	120.8 (3)
C21—C16—C15	120.4 (3)	C13—C14—H14	119.6
C17—C16—C15	121.1 (3)	C9—C14—H14	119.6
C7—C8—N2	105.6 (2)	C12—C13—C14	120.0 (3)
C7—C8—C9	134.2 (3)	C12—C13—H13	120.0
N2—C8—C9	120.2 (2)	C14—C13—H13	120.0
C18—C19—C20	117.5 (3)	C3—C4—C5	119.9 (3)
C18—C19—C22	121.1 (3)	C3—C4—H4	120.1
C20—C19—C22	121.4 (3)	C5—C4—H4	120.1
C8—C7—N1	106.3 (2)	C12—C11—C10	120.4 (3)
C8—C7—C6	132.6 (3)	C12—C11—H11	119.8
N1—C7—C6	121.2 (2)	C10—C11—H11	119.8
N2—C15—N1	106.3 (2)	C19—C18—C17	121.8 (3)
N2—C15—C16	126.8 (3)	C19—C18—H18	119.1
N1—C15—C16	126.9 (3)	C17—C18—H18	119.1
C5—C6—C1	119.1 (3)	C4—C5—C6	120.3 (3)
C5—C6—C7	120.0 (3)	C4—C5—H5	119.8
C1—C6—C7	120.9 (3)	C6—C5—H5	119.8
C2—C1—C6	120.4 (3)	C1—C2—C3	120.1 (3)
C2—C1—H1	119.8	C1—C2—H2	119.9
C6—C1—H1	119.8	C3—C2—H2	119.9
C20—C21—C16	120.4 (3)	C4—C3—C2	120.1 (3)
C20—C21—H21	119.8	C4—C3—H3	120.0
C16—C21—H21	119.8	C2—C3—H3	120.0
C9—C10—C11	120.3 (3)	C19—C22—H22A	109.5
C9—C10—H10	119.8	C19—C22—H22B	109.5
C11—C10—H10	119.8	H22A—C22—H22B	109.5
C18—C17—C16	120.0 (3)	C19—C22—H22C	109.5
C18—C17—H17	120.0	H22A—C22—H22C	109.5
C16—C17—H17	120.0	H22B—C22—H22C	109.5
C10—C9—C14	118.7 (3)	O2—N3—O3	120.7 (3)
C10—C9—C8	121.3 (3)	O2—N3—O1	118.4 (3)
C14—C9—C8	120.0 (3)	O3—N3—O1	120.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	2.05	2.905 (4)	176
N2—H2A···O2i	0.86	2.39	2.922 (3)	121
N1—H1A···O3	0.86	1.96	2.720 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	2.05	2.905 (4)	176
N2—H2A⋯O2i	0.86	2.39	2.922 (3)	121
N1—H1A⋯O3	0.86	1.96	2.720 (3)	147

Symmetry code: (i) .